Summer in Europe and Morroco

I am arriving in Zurich July 8 at 6:30 PM and will be returning to New Orleans on August 18. I am trying to determine if its cheaper to get all point to point tickets or maybe a flexi eurail pass or perhaps a regional pass (or two). Please look at the trip planned out already:

I am traveling alone on the first leg of my trip, and then meeting a friend in Freiburg, Germany and we will be traveling together from then on. The planner messed up some of the nights so the days are not accurate prior to the flight into Frankfurt.

I have reserved hostels for the nights of July 8, and 9 in Milan Italy, July 10,11, and 12 in Fez Morocco, July 14 and 15 in Essaouira, Morocco, and July 16 in Marrakesh. I plan to take the 2:30 am train from Fez to Marrakesh and transfer by bus to Essaouira arriving at 13:44 according to ONCF. I have already made deposits for these hostels with hostelbookers.com but if you think this wont work/will be too hard please give me your advice because the deposits were only a few bucks and i don’t mind changing things around for a good reason. I also wanted to venture into the rif mountains, specifically Chefchaouen. Do you guys think it would be worth it to make a day trip from fez to there and back? perhaps on the 13th and be back for the 2:30 AM train to Marrakesh. I would also feel much more comfortable if I had a local guide from fez to take me there and show me where to see and smoke the finest Chefchaouen has to offer (being safe and cautious of course). Please comment if you have any experience in the rif mountains or in Chefchaouen.

Point to point tickets i have purchased already:
Zurich HB to Milan Centrale on an EC train which arrives in Milan at 22:50 on July 8. – 30 CHF
I check out of Milan on the 10th and will take a train to Pisa that morning. I would like to have some time to see the tower before my plane departs Pisa.
Rynair flight from Pisa italy to Fez Morocco, departs at 1700 on July 10 -$41
Rynair flight from Marrakesh to Frankfurt-Hahn leaving at 9:40 and arriving at 14:25 on July 17-$53
Strassbourg, France on the TGV to Paris, arriving at 17:34, july 21-58 euro for the both of us Paris nord for Amsterdam via the Thalys train on august 28 at 6:25 am (70 euros for both).

Because we have 7 days in Paris I would like to take some day trips and maybe even stay in some cheaper cities. Im interested in Caen, Normandy, Wine country, and really any free tours that chapagne or wine makers offer.

I have also bought both of us tickets to see Iron Maiden at the Sziget festival in Budapest on August 14, so we must reach Budapest before then, and those are the only absolute dates I need to follow on this trip.
After arriving in Frankfurt I am not sure exactly what to do, I must reach frieburg by the 20th to see gogobordello with my friend there but have some options before then. I can either go straight to frieburg and chill from the 17-21, or explore that part of Germany by myself (i speak no German, but intermediate french). I am somewhat of a history and architecture buff, especially medieval and WW2 so would love to see some German castles or battlements. If you know of anything interesting to do in the area between Frankfurt and Frieburg please suggest it in addition to how to get there as cheaply as possible.

So to summarize, here are the journeys i still need tickets for:

* Zurich airport to Zurich HB
* Milan centrale (the hostel i booked is close to this station) to Pisa airport
* All travel in Morocco
* Frankfurt airport to-[your suggestions here]- to Frieburg, Germany (must make it by the 20th but I am really interested in seeing castles or WW2 artifacts: Im studying to be an engineer and archeologist)
* Frieburg, Germany to Strasbourg, France.
* Amsterdam to Berlin
* Berlin to Dresden to Prague ( I would like to see Dresden for the architecture and because slaughter house 5 is my favorite book, but I can be convinced to skip Dresden for economic/time savings)
* Prague to Vienna
* Vienna to Budapest
* Budapest to wherever and back to Zurich by 10:30 on august 18th.

So what is the cheapest way to make this trip happen? Is it difficult or easy to sleep in a train or bus seat over night and should i plan on doing this?

I originally thought a 10 day global flexi pass would be good but after looking at the surcharges and reservation fees im not sure. Should i get a regional pass for Germany/eastern Europe or Benelux-Germany? Sorry for such a long post and i really appreciate you taking the time to read and help me out.

This is a good itinerary — a bit rushed for my taste — but it seems you have a pretty good plan.

Our rail guide gives a really good idea of pricing an passes. I would check that out to determine the best plan of action. You can also click “find railpass” to see some ideas. To find prices for point to point tickets, check out the local rail sites and (sometimes) bahn.de.

Some people can sleep on train and bus seats, and others can’t. I guess it’s a personal thing. Bring ear plugs.